Skip to main content
Key Specialties
Cardiology Diabetology Endocrinology Gastroenterology Geriatrics and Gerontology Gynecology and Obstetrics Hematology Infectious Disease Internal Medicine Nephrology Neurology Oncology Pediatrics Respiratory Medicine Rheumatology Surgery
Congress Coverage
2024 ACC Congress 2023 ESMO Congress 2023 EASD Congress 2023 ERS Congress 2023 ESC Congress
Clinical Collections
Advances in Alzheimer’s

Keynote webinar | Spotlight on medication adherence

LIVE: Thursday 27th June 2024, 18:00-19:30 (CEST)
Join our expert panel to discover why you need to understand the drivers of non-adherence in your patients, and how you can optimize medication adherence in your clinics to drastically improve patient outcomes.
ADVANCED SEARCH
Log in
Top
Forensic Toxicology
Published in: Forensic Toxicology 1/2014

01-01-2014 | Original Article

Identification of a synthetic cannabinoid A-836339 as a novel compound found in a product

Authors: Nozomi Uemura, Haruhiko Fukaya, Chieko Kanai, Masao Yoshida, Jun’ichi Nakajima, Misako Takahashi, Jin Suzuki, Takako Moriyasu, Dai Nakae

Published in: Forensic Toxicology | Issue 1/2014

Login to get access

Abstract

As a part of the work conducted in our laboratory, we encountered a case in which new chemical compound was contained in a certain product. This compound was found to have a molecular weight of 310 Da by liquid chromatography–mass spectrometry and gas chromatography–mass spectrometry. Accurate mass spectrometry measurements showed that the compound had an elemental composition of C16H26N2O2S. Using these mass data together with those obtained by nuclear magnetic resonance analysis and X-ray crystallographic analysis, this compound was identified as N-[3-(2-methoxyethyl)-4,5-dimethyl-2(3H)-thiazolylidene]-2,2,3,3-tetramethylcyclopropanecarboxamide, which was reported in 2009 and named A-836339. It was described as a thiazol derivative and a selective agonist of G-protein-coupled cannabinoid receptor CB2. This is the first report to identify this compound in a dubious product.
Literature
1.
2.
Uchiyama N, Kikura-Hanajiri R, Kawahara N, Haishima Y, Goda Y (2009) Identification of a cannabinoid analog as a new type of designer drug in a herbal product. Chem Pharm Bull 57:439–441PubMedCrossRef
3.
Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y (2009) Identification of a cannabimimetic indole as a designer drug in a herbal product. Forensic Toxicol 27:61–66CrossRef
4.
Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2010) Identification and quantitation of two cannabimimetic phenylacetylindoles JWH-251 and JWH-250, and four cannabimimetic naphthoylindoles JWH-081, JWH-015, JWH-200, and JWH-073 as designer drugs in illegal products. Forensic Toxicol 29:25–37CrossRef
5.
Nakajima J, Takahashi M, Seto T, Suzuki J (2011) Identification and quantitation of cannabimimetic compound JWH-250 as an adulterant in products obtained via the Internet. Forensic Toxicol 29:51–55CrossRef
6.
Nakajima J, Takahashi M, Seto T, Kanai C, Suzuki J, Yoshida M, Hamano T (2011) Identification and quantitation of two benzoylindoles AM-694 and (4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone, and three cannabimimetic naphthoylindoles JWH-210, JWH-122, and JWH-019 as adulterants in illegal products obtained via the Internet. Forensic Toxicol 29:95–110CrossRef
7.
Nakajima J, Takahashi M, Nonaka R, Seto T, Suzuki J, Yoshida M, Kanai C, Hamano T (2011) Identification and quantitation of a benzoylindole (2-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone and a naphthoylindole 1-(5-fluoropentyl-1H-indol-3-yl)-(naphthalene-1-yl)methanone (AM-2201) found in illegal products obtained via the Internet and their cannabimimetic effects evaluated by in vitro [35S]GTPγS binding assays. Forensic Toxicol 29:132–141CrossRef
8.
Nakajima J, Takahashi M, Seto T, Yoshida M, Kanai C, Suzuki J, Hamano T (2012) Identification and quantitation of two new naphthoylindole drugs-of-abuse, (1-(5-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone (AM-2202) and (1-(4-pentenyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone, with other synthetic cannabinoids in unregulated “herbal” products circulated in the Tokyo area. Forensic Toxicol 30:33–44CrossRef
9.
Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2012) Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233. AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products. Forensic Toxicol 30:114–125CrossRef
10.
Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2013) Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012. Forensic Toxicol 31:44–53CrossRef
11.
Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products. Forensic Sci Int 227:21–32PubMedCrossRef
12.
Nakajima J, Takahashi M, Seto T, Kanai C, Suzuki J, Yoshida M, Uemura N, Hamano T (2013) Analysis of azepane isomers of AM-2233 and AM-1220, and detection of an inhibitor of fatty acid amide hydrolase [3′-(aminocarbonyl)(1,1′-biphenyl)-3-yl]-cyclohexylcarbamate (URB597) obtained as designer drugs in the Tokyo area. Forensic Toxicol 31:76–85CrossRef
13.
Uchiyama N, Matsuda S, Wakana D, Kikura-Hanajiri R, Goda Y (2013) New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA) identified as designer drugs in illegal products. Forensic Toxicol 31:93–100CrossRef
14.
Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products. Forensic Toxicol 31:223–240CrossRef
15.
Bruker Daltonics (2008) Bruker suite. Bruker AXS Inc., Madison
16.
Sheldrick GM (2008) SADABS—Bruker AXS area detector scaling and absorption, version 2008/1. University of Göttingen, Göttingen
17.
Sheldrick GM (1997) SHELXS-97, program for crystal structure solution. University of Göttingen, Göttingen
18.
Sheldrick GM (1997) SHELXL-97, program for crystal structure refinement. University of Göttingen, Göttingen
19.
Choi H, Heo S, Kim E, Hwang BY, Lee C, Lee J (2013) Identification of (1-pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone and its 5-pentyl fluorinated analog in herbal incense seized for drug trafficking. Forensic Toxicol 31:86–92
20.
Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Morzherin Y, Shafran Y (2013) Identification and analytical properties of new synthetic cannabimimetics bearing 2,2,3,3-tetramethylcyclopropanecarbonyl moiety. Forensic Sci Int 226:62–73PubMedCrossRef
21.
Zuba D, Geppert B, Sekuła K, Żaba C (2013) [1-(Tetrahydropyran-4-ylmethyl)-1H-indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone: a new synthetic cannabinoid identified on the drug market. Forensic Toxicol 31:281–291CrossRef
22.
Yao BB, Hsieh G, Daza AV, Fan Y, Grayson GK, Garrison TR, El Kouhen O, Hooker BA, Pai M, Wensink EJ, Salyers AK, Chandran P, Zhu CZ, Zhong C, Ryther K, Gallagher ME, Chin C-L, Tovcimak AE, Hradil VP, Fox GB, Dart MJ, Honore P, Meyer MD (2009) Characterization of a cannabinoid CB2 receptor-selective agonist, A-836339 [2,2,3,3-tetramethylcyclopropanecarboxylic acid [3-(2-methoxy-ethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]-amide], using in vitro pharmacological assays, in vivo pain models, and pharmacological magnetic resonance imaging. J Pharmacol Exp Ther 328:141–151PubMedCrossRef
Metadata
Title
Identification of a synthetic cannabinoid A-836339 as a novel compound found in a product
Authors
Nozomi Uemura
Haruhiko Fukaya
Chieko Kanai
Masao Yoshida
Jun’ichi Nakajima
Misako Takahashi
Jin Suzuki
Takako Moriyasu
Dai Nakae
Publication date
01-01-2014
Publisher
Springer Japan
Published in
Forensic Toxicology / Issue 1/2014
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-013-0201-x

Other articles of this Issue 1/2014

Forensic Toxicology 1/2014 Go to the issue

Original Article

Analysis of 11-nor-9-carbonyl-∆9-tetrahydrocannabinol in human blood and bile by liquid chromatography–tandem mass spectrometry after derivatization with ethyl chloroformate and amines

Original Article

Time-course profile of urinary excretion of intravenously administered α-pyrrolidinovalerophenone and α-pyrrolidinobutiophenone in a human

Erratum

Erratum to: Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products

Short Communication

Application of modified QuEChERS method to liver samples for forensic toxicological analysis

Original Article

A simple method for the simultaneous determination of mushroom toxins by liquid chromatography–time-of-flight mass spectrometry

Original Article

Rapid and simultaneous extraction of acidic and basic drugs from human whole blood for reliable semi-quantitative NAGINATA drug screening by GC–MS